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Merck
CN

158496

Proton-sponge®

99%

Synonym(s):

1,8-Bis(dimethylamino)naphthalene, N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine

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About This Item

Linear Formula:
C10H6[N(CH3)2]2
CAS Number:
20734-58-1
Molecular Weight:
214.31
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24849762
EC Number:
244-001-6
Beilstein/REAXYS Number:
396782
MDL number:
MFCD00003920
Assay:
99%
Form:
solid

Key Documents

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InChI key

GJFNRSDCSTVPCJ-UHFFFAOYSA-N

InChI

1S/C14H18N2/c1-15(2)12-9-5-7-11-8-6-10-13(14(11)12)16(3)4/h5-10H,1-4H3

SMILES string

CN(C)c1cccc2cccc(N(C)C)c12

assay

99%

form

solid

mp

49-51 °C (lit.)

solubility

chloroform: soluble 50 mg/mL, clear (faint yellow to dark yellow to dark red)

functional group

amine

Quality Level

200

Related Categories

General description

Proton-sponge is a nucleophilic base used in alkoxycarbonylation, dehydrofluorination, arylation, and intramolecular cyclization reactions.

Proton-sponge is also referred to as 1,8-dimethylamino naphthalene. It is very strong base with weak nucleophilic character due to steric effects. It also participates in the reactions between arachno-6,9-C2B8H14 and selected acyl chlorides. It has been tested as an effective H+ scavenger.

Application

Proton-sponge can be used in the synthesis of C-substituted t-BuNH-8,9-R,R′-nido-7,8,9-C3B8H9 (R,R′ = H,H; MeH; Me,Me; Ph,H and Ph,Ph) tricarbollide compounds. It was also used in the preparation of saturated fluoroalkyl(hydrido) complexes of Iridium.
Very strong base with weak nucleophilic character due to steric effects.

Legal Information

Proton-sponge is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN5179
BCCD9416
BCCJ1184
BCCJ2766
BCCH3472

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Mario Bakardjiev et al.
Dalton transactions (Cambridge, England : 2003), 39(17), 4186-4190 (2010-04-15)
Treatment of C-substituted nido dicarbadecaboranes 5,6-R',R-5,6-C(2)B(8)H(10) (1) (where R',R = H,H (1a); H,Me, (1b); Me,Me, (1c); H,Ph, (1d) and Ph,Ph, (1e) with 1,8-bis-(dimethylamino)naphthalene (proton sponge = PS) and t-BuNC in CH(2)Cl(2), followed by acidification, generated a series of pure neutral
Unusual Reactivity of ?Proton Sponge? as a Hydride Donor to Transition Metals: Synthesis and Structural Characterization of Fluoroalkyl (hydrido) Complexes of Iridium (III) and Rhodium (III).
Hughes RP, et al.
Organometallics, 20(14), 3190-3197 (2014)
1, 8-Bis (dimethylamino) naphthalene
Barner BA
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Mario Bakardjiev et al.
Inorganic chemistry, 52(15), 9087-9093 (2013-07-28)
Reactions between arachno-6,9-C2B8H14 (1) and selected acyl chlorides, RCOCl, in the presence of PS (PS = "proton sponge", 1,8-dimethylamino naphthalene) in CH2Cl2 for 24 h at reflux, followed by in situ acidification with concentrated H2SO4 at 0 °C, generate a
Nanocluster Formation and Stabilization Fundamental Studies. 2. Proton Sponge as an Effective H^+ Scavenger and Expansion of the Anion Stabilization Ability Series.
Ozkar S and Finke RG.
Langmuir, 18(20), 7653-7662 (2002)
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